100573-23-7Relevant academic research and scientific papers
Addition of tert-Butyldimethyl- or tert-Butyldiphenylsilyl Cyanide to Hindered Ketones
Golinski, Miroslaw,Brock, Carolyn P.,Watt, David S.
, p. 159 - 164 (1993)
The addition of trimethylsilyl cyanide (TMSCN), tert-butyldimethylsilyl cyanide (TBDMSCN) or tert-butyldiphenylsilyl cyanide (TBDPSCN) to sterically hindered ketones proceeded in good yield under catalysis by Lewis acids (ZnI2, CH2Cl2, 25 deg C) or bases
Rapid additions of bulky tert-butyldimethylsilyl cyanide to hindered ketones promoted by heterogeneous tin ion-exchanged montmorillonite catalyst
Wang, Jiacheng,Masui, Yoichi,Hattori, Taiki,Onaka, Makoto
experimental part, p. 1978 - 1981 (2012/05/05)
Tin ion-exchanged montmorillonite (Sn-Mont) was found to be a powerful heterogeneous catalyst for the cyanosilylation of various ketones including congested ones with a bulky cyanide source, tert-butyldimethylsilyl cyanide (TBDMSCN), giving the corresponding cyanohydrin tert-butyldimethylsilyl ethers in good (85%) to excellent (>98%) yields at room temperature. Compared to the previously reported catalysts, Sn-Mont is easy to prepare, environmentally benign, nontoxic, noncorrosive, and recyclable.
Robust and efficient, yet uncatalyzed, synthesis of trialkylsilyl-protected cyanohydrins from ketones
Cabirol, Fabien L.,Lim, Angela E. C.,Hanefeld, Ulf,Sheldon, Roger A.,Lyapkalo, Ilya M.
, p. 2446 - 2449 (2008/09/19)
(Chemical Equation Presented) High-yielding cyanosilylation of ketones with NaCN and various chlorotrialkylsilanes in DMSO proceeds smoothly without catalysis to give silyl-protected ketone cyanohydrins. The unique role of DMSO consists in rendering naked
P(RNCH2CH2)N: Efficient catalysts for the cyanosilylation of aldehydes and ketones
Fetterly, Brandon M.,Verkade, John G.
, p. 8061 - 8066 (2007/10/03)
The 1,2-addition of trialkylsilylcyanides to aldehydes and ketones produces the corresponding protected cyanohydrins in good to excellent yields when carried out at 0°C to room temperature in the presence of catalytic amounts of the nonionic strong base P(RNCH2CH2)N (R = Me, i-Pr) in THF. These catalysts are easily removed from the product by hydrolysis or column filtration through silica gel.
Trimethylsilyl Cyanide - A Reagent for Umpolung, XI. On the Ambident Character of Substituted Allylic Anions.
Huenig, Siegfried,Reichelt, Helmut
, p. 1772 - 1800 (2007/10/02)
The dependence of the α/γ-ratio of alkylation products on several factors has been determined with 1-cyano-3-aryl-1-(trimethylsiloxy)allylic anions.Increasing amounts of γ-product are found in more polar solvents, with larger alkali ions, on addition of HMPT, with smaller alkyl groups in the electrophile, and especially with p-cyanophenyl groups.In contrast, temperature and leaving groups have minor effects.On substitution of the O-silyl group by O-methyl and O-ethoxycarbonyl, α-alkylation predominates strongly.The results are compared to known allylic anions.Furthermore, the isomerisation of compounds of type C to type B is described as well as a new addition reaction of cyanoformates to aldehydes.
